Benzoic acid (2S,3S,4R,6S)-6-((2R,3R)-3-benzyloxy-2-methoxy-5,5,6-trimethyl-4-oxo-hept-6-enyl)-2-bromomethyl-4-methoxy-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Benzoic acid (2S,3S,4R,6S)-6-((2R,3R)-3-benzyloxy-2-methoxy-5,5,6-trimethyl-4-oxo-hept-6-enyl)-2-bromomethyl-4-methoxy-tetrahydro-pyran-3-yl ester
CAS No.:674769-43-8
Molecular Formula:C₃₂H₄₁BrO₇
Molecular Weight:617.577
Hs Code.:

Synonyms:Benzoic acid (2S,3S,4R,6S)-6-((2R,3R)-3-benzyloxy-2-methoxy-5,5,6-trimethyl-4-oxo-hept-6-enyl)-2-bromomethyl-4-methoxy-tetrahydro-pyran-3-yl ester

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Chemical Property of Benzoic acid (2S,3S,4R,6S)-6-((2R,3R)-3-benzyloxy-2-methoxy-5,5,6-trimethyl-4-oxo-hept-6-enyl)-2-bromomethyl-4-methoxy-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (2S,3S,4R,6S)-6-((2R,3R)-3-benzyloxy-2-methoxy-5,5,6-trimethyl-4-oxo-hept-6-enyl)-2-bromomethyl-4-methoxy-tetrahydro-pyran-3-yl ester

There total 14 articles about Benzoic acid (2S,3S,4R,6S)-6-((2R,3R)-3-benzyloxy-2-methoxy-5,5,6-trimethyl-4-oxo-hept-6-enyl)-2-bromomethyl-4-methoxy-tetrahydro-pyran-3-yl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

: 420-37-1
trimethoxonium tetrafluoroborate

: 674769-36-9
Benzoic acid (2S,3S,4R,6R)-6-((2R,3R)-3-benzyloxy-2-hydroxy-5,5,6-trimethyl-4-oxo-hept-6-enyl)-2-bromomethyl-4-methoxy-tetrahydro-pyran-3-yl ester

: 674769-43-8
Benzoic acid (2S,3S,4R,6S)-6-((2R,3R)-3-benzyloxy-2-methoxy-5,5,6-trimethyl-4-oxo-hept-6-enyl)-2-bromomethyl-4-methoxy-tetrahydro-pyran-3-yl ester

Guidance literature:: With Proton Sponge;
DOI:10.1021/ol036393z

Reference yield:

: 5072-70-8
1-bromo-2,3-dimethyl-2-butene

: 674769-43-8
Benzoic acid (2S,3S,4R,6S)-6-((2R,3R)-3-benzyloxy-2-methoxy-5,5,6-trimethyl-4-oxo-hept-6-enyl)-2-bromomethyl-4-methoxy-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 69 percent / SnCl₂*H₂O; NaI

2: 99 percent / LDA

3: BF₃*Et₂O / CH₂Cl₂ / -20 - 0 °C

4: 90 percent / proton sponge

With Proton Sponge; boron trifluoride diethyl etherate; sodium iodide; tin(ll) chloride; lithium diisopropyl amide; In dichloromethane; 1: Barbier-type reaction / 1: Swern oxidation / 3: Mukaiyama aldol reaction;
DOI:10.1021/ol036393z

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 674769-43-8
Benzoic acid (2S,3S,4R,6S)-6-((2R,3R)-3-benzyloxy-2-methoxy-5,5,6-trimethyl-4-oxo-hept-6-enyl)-2-bromomethyl-4-methoxy-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: TsOH

2.1: 90 percent / NaH

3.1: 99 percent / NBS; BaCO₃ / CCl₄ / Heating

4.1: 95 percent / TMSOTf / acetonitrile / -20 °C

5.1: OsO₄; NMO

5.2: 96 percent / NaIO₄

6.1: BF₃*Et₂O / CH₂Cl₂ / -20 - 0 °C

7.1: 90 percent / proton sponge

With N-Bromosuccinimide; osmium(VIII) oxide; N-methyl-2-indolinone; Proton Sponge; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium hydride; toluene-4-sulfonic acid; barium carbonate; In tetrachloromethane; dichloromethane; acetonitrile; 6.1: Mukaiyama aldol reaction;
DOI:10.1021/ol036393z